The present invention relates to novel uracil derivatives and herbicides having an selectivity and containing the uracil derivatives as active ingredients.
A large variety of herbicides have been prepared and practically used for protecting important crop plants such as rice, soybean, wheat, corn, cotton, beet, etc., from weeds and for enhancing productivity of these crop plant. The herbicides may be roughly classified into the following three types according to the locality of application: 1 herbicides for upland cropping, 2 herbicides for paddy field and 3 herbicides for nonarable land. Each kind of herbicides can be further classified into subclasses such as soil incorporation treatment type, pre-emergence treatment type and post-emergence treatment type (foliage treatment) according to the method of application.
With increase of global population in recent years, there is no denying the fact that productivity of principal crop plants gives a serious influence to food economy of each country, and thus enhancement of productivity of principal crop plants is now a matter of paramount importance. In fact, for the people engaged in farming, it is still more necessary to develop herbicides which are capable of economical and efficient killing or controlling of growth of weeds which do harm to cultivation of crop plants.
As such herbicides, there are demanded the ones which can meet the following requirements:
(1) Herbicidal effect is high with small amount of application. (It is necessary, especially from the viewpoint of environmental protection, to kill the weeds by application of as small as amount of herbicide as possible.) PA0 (2) Residual effect is appropriate. (Recently, the problem is pointed out that the chemicals retaining their effect in soil for a long time could give damage to the next crop plants. It is thus important that the chemicals keep an appropriate residual effect after application). PA0 (3) Weeds are killed quickly after application. (It is made possible to perform seeding and transplantation of the next crop plant in a short time after chemicals treatment.) PA0 (4) The number of times of herbicide treatment (application) required is small. (It is of much account for the farmers that the number of times of weed-controling work be minimized.) PA0 (5) Weeds killed or controlled by one of herbicide is of wide range. (It is desirable that different weeds such as broad-leaved weeds, graminaceous weeds and perennial weeds can be killed or controlled by application of one of herbicide.) PA0 (6) The application method is diversified. (The herbicidal effect is intensified when it can be applied in various ways, such as soil treatment, foliage treatment, etc.) PA0 (7) No damage to crop plants is given. (In a cultivated field where both crop plants and weeds co-exist, it is desirable that weeds alone are killed selectively by a herbicide.) PA0 (i) when R.sup.5 and R.sup.6 are taken separately, PA0 (ii) when R.sup.5 and R.sup.6 form a ring,
Nevertheless, there is yet available no herbicide which can meet all of the above requirements.
It is known that certain compounds of uracil derivatives have a herbicidal activity. For instance, in the Pesticide Manual, 8th Ed., p. 89 (published by The British Crop Protection Council, 1987), Bromacil as one the herbicides having uracil skeleton is disclosed.
There are also known the following hetero-ring derivatives which can serve as active ingredient for herbicides:
(1) 3-Aryluracil-alkyl, alkenyl and alkinylenol ethers represented by the following general formula: ##STR1## wherein R.sup.1 represents C.sub.1-8 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.2-8 alkoxyalkyl or ##STR2## R.sup.2 represents halogen or cyano, R.sup.3 represents hydrogen or halogen, R.sup.4 represents hydrogen, fluorine or C.sub.1-4 alkyl, R.sup.5 represents C.sub.1-4 alkyl or C.sub.1-4 haloalkyl, or R.sup.4 and R.sup.5 may combine to represent tri- or tetra-methylene (in which R.sup.6 and R.sup.7 represent independently C.sub.1-4 alkyl, and m is 1 or 2), and X is O, O--C(O), O--C(O)--O or C(O)--O (Japanese Patent Application Laid-Open (Kokai) No. 63-107967).
(2) Compounds represented by the following general formula: ##STR3## wherein R.sup.1 represents hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, formyl or C.sub.2-6 alkanonyl, R.sup.2 represents ether or a residue containing (thio)carbonyloxy or sulfonyloxy, the residue being directly linked to benzene nucleus A through oxygen atom, R.sup.3 represents halogen or cyano, R.sup.4 represents hydrogen or halogen, R.sup.5 represents hydrogen, halogen or C.sub.1-4 alkyl, and R.sup.6 represents C.sub.1-4 alkyl or C.sub.1-4 haloalkyl, or R.sup.5 and R.sup.6 may be combined together to represent tri- or tetrametylene, and salts of the compounds of the said formula wherein R.sup.1 is hydrogen (Japanese Patent Application Laid-Open (Kokai) No. 63-41466).
(3) Benzothiazolone derivatives represented by the general formula: ##STR4## wherein R represents hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower alkoxy-lower alkyl, lower alkoxy-lower alkoxy-lower alkyl, cinnamyl or lower cyanoalkyl (Japanese Patent Application Laid-Open (Kokai) No. 62-155276).
(4) Condensed hetero-ring derivatives represented by the general formula: ##STR5## wherein X represents oxygen atom or sulfur atom, and Z represents ##STR6## in which G represents hydrogen atom or halogen atom, A represents halogen atom or NO.sub.2, E represents hydrogen atom, halogen atom, C.tbd.N, NO.sub.2, NH.sub.2, OH, SH, OR.sub.1 [wherein R.sub.1 represents C.sub.1-5 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl-(C.sub.1-2) alkyl, C.sub.2-4 alkenyl, C.sub.3-4 alkynyl, ##STR7## (in which Q.sub.a and Q.sub.b represent independently oxygen atom or sulfur atom, R.sub.1a represents hydrogen atom or C.sub.1-3 alkyl, and R.sub.1b represents hydrogen atom, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.3-5 alkynyl, C.sub.2-3 haloalkyl, C.sub.1-2 alkoxy-(C.sub.1-2) alkyl, C.sub.3-4 cycloalkyl-(C.sub.1-2) alkyl, C.sub.3-6 cycloalkyl, CH.sub.2 CO.sub.2 --(C.sub.1-3 alkyl), or CH(CH.sub.3)--CO.sub.2 --(C.sub.1-2 alkyl), or R.sub.1a and R.sub.1b are combined to form a 4- to 6-membered ring lactone constituted by methylene chain), ##STR8## (in which R.sub.1a and Q.sub.a are the same meaning as defined above, and R.sub.1c and R.sub.1d represent independently hydrogen atom, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.3-5 alkynyl, C.sub.2-5 haloalkyl, C.sub.3-6 cycloalkyl or C.sub.3-6 cycloalkyl-(C.sub.1-2) alkyl, or R.sub.1d and R.sub.1c are combined to form a 5- to 7-membered ring constituted by methylene chain), CH2C.tbd.N, tetrahydropyranyl, tetrahydrothiopyranyl, CH.sub.2 COR.sub.1e, ##STR9## (in which R.sub.1e represents C.sub.1-3 alkyl, R.sub.1f represents hydrogen atom, C.sub.1-3 alkyl, CH.sub.2 CO.sub.2 --(C.sub.1-3) alkyl or COCH.sub.3), or C.sub.1-2 alkoxy-(C.sub.1-2) alkyl], SR.sub.3 (in which R.sub.3 is the same meaning as R.sub.1 described above), CO.sub.2 R.sup.5 (in which R.sub.5 represents hydrogen atom, C.sub.1-5 alkyl, C.sub.3-6 cycloalkyl or C.sub.3-6 cycloalkyl-(C.sub.1-2) alkyl), NHR.sub.6 (in which R.sub.6 represents C.sub.1-5 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl -(C.sub.1-2) alkyl, C.sub.2-4 alkenyl or C.sub.3-4 alkynyl), or CH.dbd.NOR.sup.7 (in which R.sup.7 is hydrogen atom, C.sub.1-5 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl-(C.sub.1-2) alkyl, C.sub.2-4 alkenyl or C.sub.3-4 alkynyl), L represents hydrogen atom or halogen atom, Y represents oxygen atom or sulfur atom, n is 0 or 1, and J represents hydrogen atom, halogen atom, C.sub.1-5 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl-(C.sub.1-2) alkyl, C.sub.2-4 alkenyl, C.sub.3-4 alkynyl, C.sub.1-5 haloalkyl, C.sub.3-4 haloalkenyl, C.sub.3-4 haloalkynyl, C.sub.1-2 alkoxy-(C.sub.1-2) alkyl, CH.sub.2 C.tbd.N, CH.sub.2 CO.sub.2 R.sub.8 (in which R.sub.8 is hydrogen atom, C.sub.1-5 alkyl, C.sub.3-6 cycloalkyl or C.sub.3-6 cycloalkyl-(C.sub.1-2) alkyl), or CH.sub.2 CH.sub.2 CO.sub.2 R.sub.9 (in which R.sub.9 is hydrogen atom, C.sub.1-5 alkyl, C.sub.3-6 cycloalkyl or C.sub.3-6 cycloalkyl-(C.sub.1-2) alkyl) (Japanese Patent Application Laid-Open (Kokai) No. 1-250388).
(5) Compounds represented by the following formula: ##STR10## wherein R.sup.1 represents hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.2-6 alkoxyalkyl, formyl, C.sub.2-6 alkanoyl or C.sub.2-6 alkoxycarbonyl; R.sup.2 represents hydrogen, C.sub.1-6 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl or C.sub.2-6 alkoxyalkyl; R.sub.3 represents halogen or nitro; R.sup.4 represents hydrogen or halogen; R.sup.5 represents hydrogen, halogen, C.sub.1-4 alkyl, chloromethyl, bromomethyl, hydroxymethyl, (C.sub.1-5 alkoxy)methyl, (C.sub.1-5 alkylthio)methyl, cyano, nitro or thiocyanato; R.sup.6 represents hydrogen, C.sub.1-4 alkyl or C.sub.1-4 fluoroalkyl, or R.sup.5 and R.sup.6 are combined to represent tri- or tetramethylene, in which one of the said methylene groups may be substituted with oxygen or sulfur, or these groups may be substituted with C.sub.1-3 alkyl; and X represents oxygen or sulfur, in which (i) when R.sup.5 is fluorine, R.sup.6 is C.sub.1-4 alkyl or C.sub.1-4 fluoroalkyl, and (ii) when R.sup.5 is cyano, R.sup.6 is hydrogen or C.sub.1-4 alkyl, and X is oxygen, and salts of the compounds of the said formula wherein R.sup.1 and/or R.sup.2 represent(s) hydrogen (Japanese Patent Application Laid-Open (Kokai) No. 61-221178).
(6) Tetrahydrophthalimide derivatives represented by the following formula: ##STR11## wherein R.sup.1 represents C.sub.1-5 alkyl, C.sub.3-5 alkenyl, C.sub.3-5 alkynyl or C.sub.1-3 alkoxymethyl, X is hydrogen, fluorine or chlorine, and A represents ##STR12## (in which R.sup.2 represents hydrogen or methyl, R.sub.3 represents hydrogen or methyl, and nitrogen atom is bonded to benzene ring (Japanese Patent Application Laid-Open (Kokai) No. 61-85385).
(7) Tetrahydrophthalimide derivatives represented by the following formula: ##STR13## wherein R.sup.1 represents alkyl, alkenyl, alkynyl, alkoxyalkyl or alkoxyalkoxyalkyl, and R.sup.2 represents hydrogen or methyl (Japanese Patent Application Laid-Open (Kokai) No. 61-30586).
(8) Tetrahydrophthalimide derivatives represented by the following formula: ##STR14## wherein R.sup.1 represents alkyl, alkenyl, alkynyl, alkoxyalkyl or alkoxyalkoxyalkyl, and R.sup.2 represents hydrogen or methyl (Japanese Patent Application Laid-Open (Kokai) No. 61-76486).
(9) Tetrahydrophthalimide derivatives represented by the following formula: ##STR15## wherein R represents C.sub.1-5 alkyl, C.sub.3-5 alkenyl, C.sub.3-5 alkynyl or C.sub.1-3 alkoxymethyl, and X represents hydrogen or fluorine (Japanese Patent Application Laid-Open (Kokai) No. 61-43188).
(10) Herbicidal compounds having the general formula: ##STR16## wherein X is hydrogen or hydroxy, R.sup.1 is hydrogen or halo and R.sup.2 is alkyl, cycloalkyl, phenyl, alkenyl, and substituted derivatives of the above (U.S. Pat. No. 3,981,715).
(11) Herbicidal compounds having the general formula: ##STR17## wherein X is hydrogen or hydroxy, R.sup.1 is hydrogen or halo and R.sup.2 is alkyl, cycloalkyl, phenyl, alkenyl, and substituted derivatives of the above (U.S. Pat. No. 3,869,457).
(12) Compounds of formula: ##STR18## wherein R.sup.1 represents hydrogen, C.sub.1-4 alkyl, C.sub.3-4 alkenyl, C.sub.3-4 alkynyl or C.sub.1-4 haloalkyl, R.sup.2 represents ##STR19## or, when R.sup.1 represents haloalkyl, hydrogen, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl or C.sub.2-8 alkoxyalkyl, R.sup.3 represents halogen or cyano, R.sup.4 represents hydrogen or halogen and R.sup.5 represents hydrogen, fluorine or C.sub.1-4 haloalkyl, as well as their enol ethers and salts (WO 88/10254).
Keen request is heard for the presentation of a herbicide which can meet the above-mentioned requirements (1)-(7), namely a herbicide which shows selectivity in potency, with no fear of giving any damage to crop plants (crop injury), exhibits excellent herbicidal effect at low dosage against a vide variety of weeds, and is also capable of exhibiting desired effect in both soil treatment and foliage treatment.
As a result of the present inventors' extensive studies, it has been found that the uracil derivatives having a haloalkyl group at the 6-position and a phenyl group at the 3-position which has a specific substituent, which are represented by the following formula (I) have penetrative translocation activity and a very high herbicidal activity, and as compared with the conventional herbicidal compounds, the said uracil derivatives can be applied for either soil treatment or foliage treatment, thereby producing a quick and high herbicidal effect even at a very low dosage against a large variety of weeds including perennial weeds, and have the property to residual effect for an appropriate period of time. The present invention was attained on the basis of the said finding.